 
data_marc 
  
_audit_creation_method            SHELXL-2013 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C17 H20 O4' 
_chemical_formula_weight          288.33 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            15 
_space_group_name_H-M_alt         'C 2/c' 
_space_group_name_Hall            '-C 2yc' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x, y, -z+1/2' 
 'x+1/2, y+1/2, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y, z-1/2' 
 '-x+1/2, -y+1/2, -z' 
 'x+1/2, -y+1/2, z-1/2' 
  
_cell_length_a                    24.445(7) 
_cell_length_b                    7.241(2) 
_cell_length_c                    17.657(5) 
_cell_angle_alpha                 90 
_cell_angle_beta                  101.424(4) 
_cell_angle_gamma                 90 
_cell_volume                      3063.3(16) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     200(2) 
_cell_measurement_reflns_used     2803 
_cell_measurement_theta_min       2.35 
_cell_measurement_theta_max       27.58 
  
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.250 
_exptl_crystal_F_000              1232 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.600 
_exptl_crystal_size_mid           0.557 
_exptl_crystal_size_min           0.440 
_exptl_absorpt_coefficient_mu     0.088 
_shelx_estimated_absorpt_T_min    0.949 
_shelx_estimated_absorpt_T_max    0.962 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.6892  
_exptl_absorpt_correction_T_max   0.7456  
_exptl_absorpt_process_details    'APEX2 (Bruker, 2007)' 
  
_exptl_special_details 
; 
Data collection is performed with four batch runs at 
φ = 0.00 ° (600 frames), at φ = 90.00 ° 
(600 frames), at φ = 180 ° (600 frames) and 
at φ = 270 ° (600 frames). 
Frame width = 0.30 \& in ω. Data is 
merged, corrected for decay, and treated with 
multi-scan absorption corrections. 
; 
  
_diffrn_ambient_temperature       200(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  8.33 
_diffrn_reflns_number             9710 
_diffrn_reflns_av_unetI/netI      0.0296 
_diffrn_reflns_av_R_equivalents   0.0254 
_diffrn_reflns_limit_h_min        -29 
_diffrn_reflns_limit_h_max        31 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -22 
_diffrn_reflns_limit_l_max        23 
_diffrn_reflns_theta_min          2.354 
_diffrn_reflns_theta_max          27.650 
_diffrn_reflns_theta_full         25.000 
_diffrn_measured_fraction_theta_max   0.986 
_diffrn_measured_fraction_theta_full  0.993 
_diffrn_reflns_Laue_measured_fraction_max    0.986 
_diffrn_reflns_Laue_measured_fraction_full   0.993 
_diffrn_reflns_point_group_measured_fraction_max   0.986 
_diffrn_reflns_point_group_measured_fraction_full  0.993 
_reflns_number_total              3528 
_reflns_number_gt                 2872 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
  
_refine_special_details 
; 
 ? 
; 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
; 
 w=1/[σ²(Fo²)+(0.0706P)²+1.5021P] 
 where P=(Fo²+2Fc²)/3 
; 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          3528 
_refine_ls_number_parameters      194 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0551 
_refine_ls_R_factor_gt            0.0451 
_refine_ls_wR_factor_ref          0.1283 
_refine_ls_wR_factor_gt           0.1208 
_refine_ls_goodness_of_fit_ref    1.039 
_refine_ls_restrained_S_all       1.039 
_refine_ls_shift/su_max           0.005 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.20309(4) 0.55874(15) 0.91532(7) 0.0371(3) Uani 1 1 d . . . . . 
O2 O 0.11487(4) 0.55656(13) 0.84808(5) 0.0256(2) Uani 1 1 d . . . . . 
O3 O 0.06489(4) 0.51542(14) 1.00077(6) 0.0324(3) Uani 1 1 d . . . . . 
O4 O -0.02255(4) 0.77046(14) 0.92759(6) 0.0296(3) Uani 1 1 d . . . . . 
H4A H -0.0283 0.6768 0.9530 0.044 Uiso 1 1 calc R U . . . 
C1 C 0.12121(5) 0.93410(17) 0.93137(7) 0.0202(3) Uani 1 1 d . . . . . 
C2 C 0.13223(5) 0.72922(17) 0.96465(7) 0.0198(3) Uani 1 1 d . . . . . 
C3 C 0.07410(5) 0.65972(18) 0.96945(7) 0.0211(3) Uani 1 1 d . . . . . 
C4 C 0.03314(5) 0.79458(18) 0.93380(7) 0.0212(3) Uani 1 1 d . . . . . 
C5 C 0.05775(5) 0.94453(18) 0.91078(8) 0.0218(3) Uani 1 1 d . . . . . 
C6 C 0.11939(6) 0.93561(19) 0.78593(8) 0.0291(3) Uani 1 1 d . . . . . 
H6A H 0.0814 0.8987 0.7776 0.035 Uiso 1 1 calc R U . . . 
C7 C 0.14499(8) 0.9573(2) 0.72285(10) 0.0392(4) Uani 1 1 d . . . . . 
H7A H 0.1245 0.9346 0.6721 0.047 Uiso 1 1 calc R U . . . 
C8 C 0.20015(8) 1.0118(3) 0.73383(10) 0.0445(4) Uani 1 1 d . . . . . 
H8A H 0.2177 1.0272 0.6908 0.053 Uiso 1 1 calc R U . . . 
C9 C 0.22954(7) 1.0436(3) 0.80795(11) 0.0428(4) Uani 1 1 d . . . . . 
H9A H 0.2675 1.0804 0.8158 0.051 Uiso 1 1 calc R U . . . 
C10 C 0.20402(6) 1.0221(2) 0.87116(9) 0.0317(3) Uani 1 1 d . . . . . 
H10 H 0.2247 1.0453 0.9217 0.038 Uiso 1 1 calc R U . . . 
C11 C 0.14840(6) 0.96691(17) 0.86107(8) 0.0226(3) Uani 1 1 d . . . . . 
C12 C 0.14100(6) 1.0817(2) 0.99373(9) 0.0304(3) Uani 1 1 d . . . . . 
H12A H 0.1345 1.2049 0.9708 0.046 Uiso 1 1 calc R U . . . 
H12B H 0.1810 1.0655 1.0146 0.046 Uiso 1 1 calc R U . . . 
H12C H 0.1202 1.0685 1.0355 0.046 Uiso 1 1 calc R U . . . 
C13 C 0.15511(5) 0.60549(17) 0.90770(8) 0.0222(3) Uani 1 1 d . . . . . 
C14 C 0.13303(7) 0.4626(2) 0.78437(9) 0.0351(4) Uani 1 1 d . . . . . 
H14A H 0.1476 0.3383 0.8008 0.042 Uiso 1 1 calc R U . . . 
H14B H 0.1631 0.5339 0.7676 0.042 Uiso 1 1 calc R U . . . 
C15 C 0.08354(9) 0.4470(3) 0.71948(10) 0.0461(4) Uani 1 1 d . . . . . 
H15A H 0.0542 0.3757 0.7367 0.069 Uiso 1 1 calc R U . . . 
H15B H 0.0945 0.3844 0.6756 0.069 Uiso 1 1 calc R U . . . 
H15C H 0.0695 0.5708 0.7037 0.069 Uiso 1 1 calc R U . . . 
C16 C 0.17066(6) 0.7121(2) 1.04405(8) 0.0307(3) Uani 1 1 d . . . . . 
H16A H 0.1553 0.7843 1.0819 0.046 Uiso 1 1 calc R U . . . 
H16B H 0.2078 0.7589 1.0413 0.046 Uiso 1 1 calc R U . . . 
H16C H 0.1734 0.5821 1.0598 0.046 Uiso 1 1 calc R U . . . 
C17 C 0.02682(6) 1.1130(2) 0.87624(9) 0.0327(3) Uani 1 1 d . . . . . 
H17A H -0.0129 1.0837 0.8600 0.049 Uiso 1 1 calc R U . . . 
H17B H 0.0417 1.1533 0.8313 0.049 Uiso 1 1 calc R U . . . 
H17C H 0.0315 1.2121 0.9148 0.049 Uiso 1 1 calc R U . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
O1 C13 1.2024(17) . ? 
O2 C13 1.3384(16) . ? 
O2 C14 1.4571(18) . ? 
O3 C3 1.2237(17) . ? 
O4 C4 1.3553(16) . ? 
O4 H4A 0.8400 . ? 
C1 C5 1.5235(18) . ? 
C1 C11 1.5381(18) . ? 
C1 C12 1.5419(19) . ? 
C1 C2 1.5987(18) . ? 
C2 C3 1.5255(17) . ? 
C2 C16 1.5301(18) . ? 
C2 C13 1.5328(19) . ? 
C3 C4 1.4500(18) . ? 
C4 C5 1.3427(18) . ? 
C5 C17 1.4995(19) . ? 
C6 C7 1.390(2) . ? 
C6 C11 1.393(2) . ? 
C6 H6A 0.9500 . ? 
C7 C8 1.381(3) . ? 
C7 H7A 0.9500 . ? 
C8 C9 1.382(3) . ? 
C8 H8A 0.9500 . ? 
C9 C10 1.391(2) . ? 
C9 H9A 0.9500 . ? 
C10 C11 1.394(2) . ? 
C10 H10 0.9500 . ? 
C12 H12A 0.9800 . ? 
C12 H12B 0.9800 . ? 
C12 H12C 0.9800 . ? 
C14 C15 1.497(2) . ? 
C14 H14A 0.9900 . ? 
C14 H14B 0.9900 . ? 
C15 H15A 0.9800 . ? 
C15 H15B 0.9800 . ? 
C15 H15C 0.9800 . ? 
C16 H16A 0.9800 . ? 
C16 H16B 0.9800 . ? 
C16 H16C 0.9800 . ? 
C17 H17A 0.9800 . ? 
C17 H17B 0.9800 . ? 
C17 H17C 0.9800 . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C13 O2 C14 116.24(11) . . ? 
C4 O4 H4A 109.5 . . ? 
C5 C1 C11 112.46(11) . . ? 
C5 C1 C12 107.26(11) . . ? 
C11 C1 C12 110.16(11) . . ? 
C5 C1 C2 102.89(10) . . ? 
C11 C1 C2 111.82(10) . . ? 
C12 C1 C2 111.99(11) . . ? 
C3 C2 C16 109.39(11) . . ? 
C3 C2 C13 107.97(10) . . ? 
C16 C2 C13 108.43(11) . . ? 
C3 C2 C1 103.62(10) . . ? 
C16 C2 C1 116.11(11) . . ? 
C13 C2 C1 110.98(10) . . ? 
O3 C3 C4 126.74(12) . . ? 
O3 C3 C2 124.30(12) . . ? 
C4 C3 C2 108.93(11) . . ? 
C5 C4 O4 125.65(12) . . ? 
C5 C4 C3 111.33(11) . . ? 
O4 C4 C3 122.99(12) . . ? 
C4 C5 C17 124.11(12) . . ? 
C4 C5 C1 112.57(11) . . ? 
C17 C5 C1 123.02(12) . . ? 
C7 C6 C11 121.30(15) . . ? 
C7 C6 H6A 119.3 . . ? 
C11 C6 H6A 119.3 . . ? 
C8 C7 C6 120.10(16) . . ? 
C8 C7 H7A 119.9 . . ? 
C6 C7 H7A 119.9 . . ? 
C7 C8 C9 119.36(15) . . ? 
C7 C8 H8A 120.3 . . ? 
C9 C8 H8A 120.3 . . ? 
C8 C9 C10 120.65(16) . . ? 
C8 C9 H9A 119.7 . . ? 
C10 C9 H9A 119.7 . . ? 
C9 C10 C11 120.70(15) . . ? 
C9 C10 H10 119.7 . . ? 
C11 C10 H10 119.7 . . ? 
C6 C11 C10 117.89(13) . . ? 
C6 C11 C1 121.57(12) . . ? 
C10 C11 C1 120.50(12) . . ? 
C1 C12 H12A 109.5 . . ? 
C1 C12 H12B 109.5 . . ? 
H12A C12 H12B 109.5 . . ? 
C1 C12 H12C 109.5 . . ? 
H12A C12 H12C 109.5 . . ? 
H12B C12 H12C 109.5 . . ? 
O1 C13 O2 124.19(13) . . ? 
O1 C13 C2 124.46(13) . . ? 
O2 C13 C2 111.35(11) . . ? 
O2 C14 C15 107.61(14) . . ? 
O2 C14 H14A 110.2 . . ? 
C15 C14 H14A 110.2 . . ? 
O2 C14 H14B 110.2 . . ? 
C15 C14 H14B 110.2 . . ? 
H14A C14 H14B 108.5 . . ? 
C14 C15 H15A 109.5 . . ? 
C14 C15 H15B 109.5 . . ? 
H15A C15 H15B 109.5 . . ? 
C14 C15 H15C 109.5 . . ? 
H15A C15 H15C 109.5 . . ? 
H15B C15 H15C 109.5 . . ? 
C2 C16 H16A 109.5 . . ? 
C2 C16 H16B 109.5 . . ? 
H16A C16 H16B 109.5 . . ? 
C2 C16 H16C 109.5 . . ? 
H16A C16 H16C 109.5 . . ? 
H16B C16 H16C 109.5 . . ? 
C5 C17 H17A 109.5 . . ? 
C5 C17 H17B 109.5 . . ? 
H17A C17 H17B 109.5 . . ? 
C5 C17 H17C 109.5 . . ? 
H17A C17 H17C 109.5 . . ? 
H17B C17 H17C 109.5 . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C5 C1 C2 C3 -7.79(12) . . . . ? 
C11 C1 C2 C3 -128.72(11) . . . . ? 
C12 C1 C2 C3 107.09(12) . . . . ? 
C5 C1 C2 C16 -127.74(12) . . . . ? 
C11 C1 C2 C16 111.33(13) . . . . ? 
C12 C1 C2 C16 -12.86(15) . . . . ? 
C5 C1 C2 C13 107.86(11) . . . . ? 
C11 C1 C2 C13 -13.06(14) . . . . ? 
C12 C1 C2 C13 -137.26(11) . . . . ? 
C16 C2 C3 O3 -46.57(18) . . . . ? 
C13 C2 C3 O3 71.24(16) . . . . ? 
C1 C2 C3 O3 -171.00(13) . . . . ? 
C16 C2 C3 C4 131.43(12) . . . . ? 
C13 C2 C3 C4 -110.77(12) . . . . ? 
C1 C2 C3 C4 7.00(13) . . . . ? 
O3 C3 C4 C5 174.64(13) . . . . ? 
C2 C3 C4 C5 -3.29(15) . . . . ? 
O3 C3 C4 O4 -3.5(2) . . . . ? 
C2 C3 C4 O4 178.59(11) . . . . ? 
O4 C4 C5 C17 1.9(2) . . . . ? 
C3 C4 C5 C17 -176.16(13) . . . . ? 
O4 C4 C5 C1 175.74(12) . . . . ? 
C3 C4 C5 C1 -2.32(16) . . . . ? 
C11 C1 C5 C4 127.01(12) . . . . ? 
C12 C1 C5 C4 -111.72(13) . . . . ? 
C2 C1 C5 C4 6.53(14) . . . . ? 
C11 C1 C5 C17 -59.06(16) . . . . ? 
C12 C1 C5 C17 62.20(16) . . . . ? 
C2 C1 C5 C17 -179.55(12) . . . . ? 
C11 C6 C7 C8 -0.3(2) . . . . ? 
C6 C7 C8 C9 0.3(3) . . . . ? 
C7 C8 C9 C10 -0.3(3) . . . . ? 
C8 C9 C10 C11 0.4(3) . . . . ? 
C7 C6 C11 C10 0.4(2) . . . . ? 
C7 C6 C11 C1 -176.99(13) . . . . ? 
C9 C10 C11 C6 -0.5(2) . . . . ? 
C9 C10 C11 C1 176.97(14) . . . . ? 
C5 C1 C11 C6 -23.64(17) . . . . ? 
C12 C1 C11 C6 -143.24(13) . . . . ? 
C2 C1 C11 C6 91.55(14) . . . . ? 
C5 C1 C11 C10 159.01(12) . . . . ? 
C12 C1 C11 C10 39.42(17) . . . . ? 
C2 C1 C11 C10 -85.79(15) . . . . ? 
C14 O2 C13 O1 -8.78(19) . . . . ? 
C14 O2 C13 C2 170.95(11) . . . . ? 
C3 C2 C13 O1 -142.83(13) . . . . ? 
C16 C2 C13 O1 -24.41(17) . . . . ? 
C1 C2 C13 O1 104.24(15) . . . . ? 
C3 C2 C13 O2 37.44(14) . . . . ? 
C16 C2 C13 O2 155.86(11) . . . . ? 
C1 C2 C13 O2 -75.49(13) . . . . ? 
C13 O2 C14 C15 -171.29(12) . . . . ? 
  
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
O4 H4A O3  0.84 1.92 2.7340(15) 162.4 5_567 
  
_refine_diff_density_max    0.343 
_refine_diff_density_min   -0.276 
_refine_diff_density_rms    0.046 
  
_shelxl_version_number 2013-2 
  
  
  
